Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 42, Pages 16794-16797Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2077813
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Funding
- EPSRC
- European Research Council [246785]
- Royal Society
- FQRNT (Quebec)
- EPSRC [EP/E052185/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/E052185/1, EP/D501725/1] Funding Source: researchfish
- European Research Council (ERC) [246785] Funding Source: European Research Council (ERC)
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The addition of an aryllithium reagent to a secondary boronic ester leads to an intermediate boron-ate complex that behaves as a chiral nucleophile, reacting with a broad range of electrophiles with inversion of stereochemistry. Depending on the electrophile, the C-B bond can be converted into C-I, C-Br, C-Cl, C-N, C-O, and C-C, all with very high levels of stereocontrol. This discovery now adds a new, readily available, configurationally stable, chiral organometallic-type reagent to the arsenal of methods for use in asymmetric organic synthesis.
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